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Poster: J.B. Nicholson-Owens Date: Mar 24, 2004 12:58am
Forum: forums Subject: Playing FLAC files. has software for playing FLAC files, either with another program (such as Winamp) or alone. The text on the bottom of the page suggests that Winamp has an official FLAC decoder and there is another FLAC decoder by Giacomo Margarito for Winamp.

I don't run Winamp so I can't offer specific help, but it seems fairly straightforward to me that if you upgrade to the latest Winamp or add Margarito's plugin you can restart Winamp and then associate .flac files with Winamp and it will play them when you double-click on them.